89129-21-5Relevant academic research and scientific papers
Synthesis and oxidative fragmentation of catharanthine analogs. Comparison to the fragmentation - Coupling of catharanthine and vindoline
Sundberg, Richard J.,Hong, Jian,Smith, Stanton Q.,Sabat, Michal,Tabakovic, Ibro
, p. 6259 - 6292 (2007/10/03)
Two new analogs of catharanthine have been synthesized in racemic form. They differ from catharanthine in the fusion of the indole ring to the non- aromatic portion of the iboga skeleton, with the [2,3] fusion present in catharanthine being replaced by [2,1] and [3,2] fusions. The corresponding deethyl analogs were also and methodological improvements were applied to an existing synthesis of deethylcatharanthine and a formal synthesis of racemic catharanthine. The reactivity of the catharanthine analogs toward coupling with vindoline was examined. Coupling was attempted by both the amine oxide fragmentation (Potier) and Fe3+ methods. Under Potier conditions the [2,1] fused analogs give low yields of coupling products in which vindaline is attached to the 3-position of the indole ring. The [3,2] isomers undergo fragmentation of the C16-C21 bond, as observed for catharanthine, but no coupling to vindoline occurs. The reactivity, oxidation potentials and conformation of the analogs are compared with catharanthine, deethylcatharanthine and N-methylcatharanthine.
2-Azabicyclo(2.2.2)octane derivatives and their use as immunosuppressive agents
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, (2008/06/13)
The invention relates to new 2-azabicyclo[2.2.2]octane derivatives of the formula (I), STR1 wherein A is hydrogen, alkoxycarbonyl having from one to 4 carbon atoms in the alkoxy group, phenylalkoxycarbonyl having from one to 4 carbon atoms in the alkoxy moiety, alkyl having from one to 6 carbon atoms, aralkyl containing from one to 4 carbon atoms in the alkyl moiety or substituted acyl, R1 is hydrogen or alkyl having from one to 4 carbon atoms, Z is hydrogen or halogen, X is hydrogen or halogen, Y is hydrogen, or X and Y together represent a C--C bond, W is alkoxycarbonyl having from one to 4 carbon atoms in the alkoxy moiety, cyano, carboxamido or haloformyl, or if X stands for halogen, X and Y together represent a STR2 group. According to another aspect of the invention there is provided a process for the preparation of the above compounds, which are pharmaceutically active, in particular, possess valuable anticonvulsive, vasodilating or gastric acid secretion inhibiting properties. Pharmaceutical compositions containing compounds of the formula (I) are also within the scope of the invention.
Indolo[2,3-a]quinolizine and indolo[2,3-g]cyclopent[a]indolizine derivatives, compositions and methods employing them for treating ulcers
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, (2008/06/13)
The invention relates to new indolo[2,3-g]cyclopent[a]indolizine derivatives of the formulae (II) STR1 and/or (III) STR2 wherein W is alkoxycarbonyl having from one to four carbon atoms in the alkoxy moiety or cyano, R1 is hydrogen or alkyl hav
Synthesis of Vinca alkaloids and related compounds XVII. Synthesis of deethylcatharanthine
Szantay,Keve,Bolcskei,Acs
, p. 5539 - 5540 (2007/10/02)
Starting from indolylacetic acid the synthesis of (±)deethylcatharanthine was achieved using fewer steps than the previous pathways.
